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382426

Sigma-Aldrich

(R)-(+)-1,1′-Bi-(2-naphthylamin)

99%

Synonym(e):

(R)-(+)-1,1′-Binaphthalin-2,2′-diamin, (R)-(+)-1,1′-Binaphthyl-2,2′-diamin, (R)-(+)-2,2′-Diamino-1,1′-binaphthalin, (R)-(+)-DABN

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About This Item

Lineare Formel:
H2NC10H6C10H6NH2
CAS-Nummer:
18741-85-0
Molekulargewicht:
284.35
Beilstein:
5279621
MDL-Nummer:
MFCD00145204
UNSPSC-Code:
12352005
PubChem Substanz-ID:
24863894
NACRES:
NA.22

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Qualitätsniveau

200

Assay

99%

Optische Aktivität

[α]20/D +157°, c = 1 in pyridine

Optische Reinheit

ee: 99% (HPLC)

mp (Schmelzpunkt)

242-244 °C (lit.)

SMILES String

Nc1ccc2ccccc2c1-c3c(N)ccc4ccccc34

InChI

1S/C20H16N2/c21-17-11-9-13-5-1-3-7-15(13)19(17)20-16-8-4-2-6-14(16)10-12-18(20)22/h1-12H,21-22H2

InChIKey

DDAPSNKEOHDLKB-UHFFFAOYSA-N

Verwandte Kategorien

Allgemeine Beschreibung

(R)-(+)-1,1′-Binaphthyl-2,2′-diamine is an axially dissymmetric binaphthyl ligand mainly used in enantioselective catalysis.[1]

Anwendung

1,1′-Binaphthyl-2,2′-diamine derivatives have been used for asymmetric hydrogenations,[2] cyclopropanations,[3][4] and formation of chiral lactones.[4][5][6]
1,1′-Binaphthyl-2,2′-diamine derivatives have been used for asymmetric hydrogenations,[2] cyclopropanations,[3][4] and formation of chiral lactones.[4][5][6] Its chiral sulphonamide, chiral diphenylphosphoramide and chiral diphenylthiophosphoramide derivatives are useful ligands for asymmetric addition reaction of diethylzinc to aldehydes in the presence of titanium(IV) alkoxide.[1]

Vorsicht

May darken in storage.

Piktogramme

Exclamation mark
GHS07

Signalwort

Warning

Gefahreneinstufungen

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Zielorgane

Respiratory system

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Persönliche Schutzausrüstung

dust mask type N95 (US), Eyeshields, Gloves

Hier finden Sie alle aktuellen Versionen:

Analysenzertifikate (COA)

Lot/Batch Number
BCBB0981
BCBB0981V
07307HH
049313/3
10404AH

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1,1'-BINAPHTHYL-8,8'-DICARBOXYLIC ACID AldrichCPR

S457000

1,1'-BINAPHTHYL-8,8'-DICARBOXYLIC ACID

(1R,2R)-(+)-1,2-Diphenylethylendiamin 97%

Sigma-Aldrich

364010

(1R,2R)-(+)-1,2-Diphenylethylendiamin

Chem. Abstr., 123, 101213k-101213k (1995)
Trifluoromethanesulfonamide, diphenylphosphoramide and diphenylthiophosphoramide of (R)-(+)-1, 1'-binaphthyl-2, 2'-diamine as chiral catalyst ligands for the titanium (IV) alkoxide-promoted addition of diethylzinc to aldehydes.
Shi M and Sui WS.
Chirality, 12(7), 574-580 (2000)
Yamamoto, Y. et al.
The Journal of Organic Chemistry, 56, 1112-1112 (1991)
Miyano, S.et al.
Bulletin of the Chemical Society of Japan, 57, 2171-2171 (1984)
The Journal of Organic Chemistry, 56, 1112-1112 (1991)

Questions

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  1. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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  2. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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